Dimethylformamide → 3-Pyridinecarboxaldehyde, 2-methoxy-4-methyl- (9CI)

Temperature

-70 °C

To a stirred solution of 5-bromo-2-methoxy-4-methylpyridine (2.6 g, 13 mmol) in dry THF (40 mL) under argon at −70° C. was added 1.6M n-BuLi in hexanes (8.1 mL, 14 mmol) over ten minutes. The mixture was stirred at −70° C. for 30 minutes and then anhydrous DMF (1.2 mL, 15 mmol) was added portion-wise at a rate that kept the temperature at −70° C. When the addition was complete, the mixture was stirred at −70° C. for 30 minutes and then at RT overnight. The reaction was quenched with 1M hydrochloric acid (40 mL) and then extracted three times with TBME. The combined organic phases were washed with brine, dried, filtered and concentrated. Column chromatography with TBME-light petroleum ether (1:1) as eluent gave 1.8 g (91%) of the title compound as pale yellow solid.

1. customat −70° C
2. additionWhen the addition
3. stirringthe mixture was stirred at −70° C. for 30 minutes
4. customat RT
5. customovernight
6. customThe reaction was quenched with 1M hydrochloric acid (40 mL)
7. extractionextracted three times with TBME
8. washThe combined organic phases were washed with brine
9. customdried
10. filtrationfiltered
11. concentrationconcentrated

ORD record

ord-77fe3ed048b348e08dda0d636ff4e9a5

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07655664B2